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Ever destroy a perfectly good pair of slip-ons by not wearing socks? It's the worst! Your feet and those shoes smell like zombie dog rotten egg shit. But if you just wore a pair of socks that zombie dog would have never showed up.

At this point, I’m deep into the plan.

Too deep to back out effectively. The fog rolls over the two riders in front of me and for a moment I think that maybe this is all a figment of my imagination−some sort of fucked up Matrix meets the world of sporty bicycle riding.

Then a car whizzes by me over my left shoulder, and I’m shaken back into the reality of the situation.

Every year I tell myself that I am going to complete the Festive 500 Challenge. But this is going to be the year where I don’t back out. The Challenge happens during the holidays, so it is the perfect excuse for a couple of things. One, escape! Two, eat! (Or at least keep eating without turning into a fat shit.) Three, excuses! The challenge comes at the weirdest time as well. The cyclocross season is pretty much over and the long, slow road to spring riding and racing is stretched out in front of you. So, during this time, when I am trying to ride a few hundred miles, I find myself pondering the same question: “What’s my motivation here?”

The challenge is to ride 500km between Christmas Eve and New Year’s Day. Seems like a pretty easy proposition, right? Let’s break that down, just so that we are clear about what it means. 500 km = 310 miles. That times out to roughly eight days. If we are still in math mode that translates to roughly 39 miles per day. Which, when you put it that way, seems like a pretty easy prospect.

It became quickly apparent that it wasn’t. But with a little help from my friends, anything is possible.

Day One:

With Max, CD, Julie and Tim 25 Miles

We start late. Later than we thought we would start. We’re waiting for each other and it’s like we have forgotten how to do long rides on a bike. Someone forgets a glove. It’s colder than anyone anticipated and the shining sun has tricked a few of us into wearing less clothes than we might have otherwise. Now we’re on a bike path and the usual game of dodging riders becomes amplified by dodging homeless that are setting up their Christmas decorations.

Day Two:

Christmas Day
0 Miles
Spouses kept happy : 1

The second day proves to be the hardest. Because my wife is also a cyclist I think she won’t mind that I sneak out in the morning for a ride, before we open presents.This doesn’t go over well. At all.

Day Three:

With Patrick & Julie
35 Miles

I convince Patrick and my wife Julie to skip work for the day and go out with me. What could really happen the day after Christmas anyway? I stop by the office to refill my bottles and suddenly feel guilty. That guilt burns away quickly as the hill turns upwards and the fog settles in. There is an eerie stillness to the West Hills as we pedal up, then down, then back up, a move I later regret when I realize that I shouldn’t be wasting time going up and down when the point of all of this is to get to that 500km. What felt like at least 50 turned out to be just 35.

Day Four:

With Simon
70 Miles

I cannot stop eating. I have dragged my friend Simon with me. The holidays have given him time off. We ride out past the airport and into Troutdale where we stop for coffees as the day is deceptively cold. However, the sun is out, and as we talk of his upcoming fatherhood, we are thankful.

Day Five:

With Steven, Joel, Simon, Leah
50 Miles

Good company helps. Good weather helps even more. Steven is up for a road ride instead of his usual mountain biking tendency. His lady is in town from SF and we decide to take her up and over Wildcat Mountain. We laugh and eat salty chips while riding our bikes and suddenly the prospect of having to do this every day doesn’t sound so bad. This high feeling is tempered by the realization that I haven’t done enough riding per day to help it even out in the long run.

Day Six:

Moving day for Eric, post-moving ride with Tim
35 Miles

Somehow, I volunteered to help Eric move during the Festive 500. I was thinking of camaraderie and brotherhood when I decided on this course of action. But my legs are tired. They remind me constantly, and I console myself by thinking “these are not even long days on the bike.” After we blast through the move – roughly 15 people make short work of it – Tim and I somehow rally ourselves and ride out to Sauvie Island. Out at Sauvie we spot our friend Michael, and he takes a picture of us. I have to continue to remind myself to take pictures and to look around, as my views are becoming increasingly inward and vision-narrowing. Tim and I have a hard conversation on the way home. We realize that tomorrow will have to be a big day to make this happen, to finish in time.

Day Seven:

With Patrick and Tim
103 miles

The prospect of a 100-mile day in the heart of December is not one that looks good. In the middle of the summer, when chamois time is tanning time, when the mere thought of being on the bike all day long brings slight patters to one’s heart, that’s when riding 100 miles is fun. When your bike is weighted down with fenders and covered in grit, it is not that fun. Tim and I eschew extra jackets for extra food (thank you – dear wife, for Nutella filled crepes) and head out along The Gorge. Patrick takes us to Crowne Point, where we bid him adieu and start down the winding road to the falls.
We make it all the way out to Charburger, the diner cum tourist trap that sits on the Oregon side of the Bridge of the Gods. We spend a few minutes stuffing too sweet cookies into our mouths before we try to head back out into the cold. I overhear the electric hand dryer in the men’s bathroom and get an idea; I remove my wool baselayer and stand there drying it. It takes nearly five cycles, but there is nothing like putting on a toasty warm baselayer for a 50-mile return trip in the cold.

This action proves to be my best idea of the week as the rain starts sputtering down on us the moment we leave the safety of the Charburger awning. I look down at Tim’s bike and then back at mine. He is not using fenders and that means that either I remain in the front of our little group of two — taking in all the rain and wind for both of us — or I get a mouthful of gritty dark water off the spray of his wheel for the next 50 miles. I choose the former and start thinking about Crowne Point and that beautiful 20-mile downhill on the other side of it.

As we start out, I curse Tim and his ineffective choice of bicycle, but this feeling quickly subsides as I console myself with the thought that I would rather have him there, even if back there, than not at all. As we navigate the tight turns below each of the falls, I’m considering everyone along the week that helped me get there. Like Ira standing atop a pile of rocks shooting photos while Leah pumps air into her tire. And Julie making food in the mornings to eat and to pack along. There’s an image of Steven jamming a bag of chips into his face, grinning the whole time. And Simon laughing as I tried to rid us of an unknown cyclist that had latched onto our wheel. Was he real? No matter what I did, I could not shake him. Even the chance meeting with Michael on his own vision quest of sorts had given another little nudge toward the finish line.

But where is that finish line?

As we rolled back into town that last day – altering our route slightly to make sure that we hit the 100-mile mark for the day – the light faded to nothing, and Tim’s rear light was the only thing preventing me from lying down for a nap on the side of the road. I had lost ten pounds, gained a nagging cough, traversed roads I’d never seen before and some that I will probably never see again. What again is my motivation? Just to finish, I guess.